Dimethylformamide → 2-Chloro-6-fluoro-3-(phenylmethoxy)benzaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-benzyloxy-2-chloro-4-fluoro-benzene (53, 5.8 g, 0.024 mol) in tetrahydrofuran (100 mL) was added 2.50 M of n-butyllithium (2.7 mL, 2.50 M in hexane, 0.029 mol) slowly at −78° C. over 15 minutes under nitrogen. The reaction mixture was stirred at −78° C. for 30 minutes. To the reaction mixture was then added N,N-dimethylformamide (4.2 mL, 0.054 mol). The reaction was allowed to warm to room temperature and was continued at room temperature overnight. The reaction mixture was poured into ice water, extracted with ethyl acetate, washed with hydrochloric acid (10%), water, brine, and dried over magnesium sulfate. After removal of solvent, the residue was purified by silica gel column chromatography eluting with ethyl acetate in hexane to provide the compound as a white solid (54, 2.1 g, 32%). MS (ESI) [M+H+]+=265.08.

Provenance & Evidence